Triethylamine → N-(2-azidoethyl)-5-(dimethylamino)naphthalene-1-sulfonamide

HRID 529918Notes

Reaction equation

HRID 529918 reaction equation
[N:1]([CH2:4][CH2:5][NH:6]C(=O)CCCCCCCCCCCCC)=[N+:2]=[N-:3].[CH3:22][N:23]([CH3:38])[C:24]1[CH:33]=[CH:32][CH:31]=[C:30]2[C:25]=1[CH:26]=[CH:27][CH:28]=[C:29]2[S:34](Cl)(=[O:36])=[O:35].N(CCN)=[N+]=[N-].C(N(CC)CC)C>ClCCl>[N:1]([CH2:4][CH2:5][NH:6][S:34]([C:29]1[C:30]2[C:25](=[C:24]([N:23]([CH3:38])[CH3:22])[CH:33]=[CH:32][CH:31]=2)[CH:26]=[CH:27][CH:28]=1)(=[O:36])=[O:35])=[N+:2]=[N-:3]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 11801Dansyl chlorideHCID 55649Ethylamine, 2-azido-HCID 57914356N-(2-azidoethyl)tetradecanamide

Product 1

HCID 16107790N-(2-azidoethyl)-5-(dimethylamino)naphthalene-1-sulfonamideYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

As in the synthesis of N-(2-azidoethyl)tetradecanamide, 5-(dimethylamino)naphthalene-1-sulfonyl chloride (0.321 g, 1.19 mmol) was reacted with 2-azidoethanamine (0.103 g, 1.19 mmol) and triethylamine (0.241 g, 2.38 mmol) in dichloromethane (5 mL) to give N-(2-azidoethyl)-5-(dimethylamino)naphthalene-1-sulfonamide (0.328 g, 86% yield). 1H NMR (300 MHz, CDCl3) δ 8.52 (d, J=8.4 Hz, 1H), δ 8.28 (d, J=8.4 Hz, 1H), δ 8.22 (d, J=0.9 Hz, 1H), δ 7.53 (t, J=8.1 Hz, 1H), δ 7.50 (t, J=7.5 Hz, 1H), δ 7.17 (d, J=7.8 Hz, 1H), δ 5.58 (t, J=1.8 Hz, 1H), δ 3.28 (t, J=5.7 Hz, 2H), δ 3.03 (q, J=6.3, 5.7 Hz, 2H), δ 2.85 (s, 6H) ppm; 13C NMR (75 MHz, CDCl3) δ 152.3, 134.8, 130.9, 130.1, 129.7, 128.9, 123.4, 118.9, 115.6, 51.0, 45.6, 42.6 ppm; HRMS (ESI) calcd for C14H17N5O2S (M+) 319.1103. found 319.1104.

Sources & evidence

ORD record
ord-8ec92b1b0fac4fa5a88dc43d7e7462b2
Source dataset
uspto-grants-2016_05
Patent number
US09351491B2

Reaction notes

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